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Solution Structure of a Dilithiumamide/Diethylzinc Heterocomplex that Catalyzes Asymmetric Alkylation Reactions
Author(s) -
Eriksson Johan,
Arvidsson Per I.,
Davidsson Öjvind
Publication year - 1999
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19990802)5:8<2356::aid-chem2356>3.0.co;2-k
Subject(s) - diethylzinc , chemistry , benzaldehyde , alkylation , lithium (medication) , stereochemistry , catalysis , organic chemistry , enantioselective synthesis , endocrinology , medicine
The solution‐state structure of the complex formed between diethylzinc and dilithiated (2 S ,5 S )‐2‐isobutyl‐5‐isopropylpiperazine was found to adopt a rigid boat conformation. NMR investigations have shown that on addition of benzaldehyde the carbonyl oxygen mainly coordinates to one of the lithium atoms (see diagram). This facilitates a chair–twisted boat–chair conformational exchange.